Best Practices for Open Communication in Onboarding

When onboarding a new team member, a recent experience with asynchronous collaboration brought a humbling revelation. As I was onboarding her to our tech stack, I uncovered a blind spot in communications within our project management software, Asana. 📝 In the meticulous notes I left for myself a while ago in one of the Asana projects, I had cut and pasted some language from an email to a client that included the word "YOU". 🤔 I failed to consider the potential confusion for my new team member. It hadn't occurred to me that she would interpret that "YOU" to be referencing her. ⚠️ What I had put in Asana as notes became unintended directives for the new Virtual Work Insider team member! The result? 📉 A cascade of actions on her end, each based on a misinterpretation of my notes. ⏳ This was an inefficient use of her time and effort that were invested in tasks that weren't needed or intended. The fix? 🔄 Once I realized what had happened we had a great discussion about how I would change my note-taking behavior in shared Asana projects to make the async communication clearer and we refined on our norms for how new requests would come through to her. My aha moment made we want to share some actionable insights for seamless onboarding in asynchronous settings. ✅ Precision in Messaging: Avoid vague language and ensure that your notes are explicitly for personal use and directives to others are clearly marked as tasks. ✅ Establish Communication Norms: Kickstart the collaboration by setting expectations on how tools like Asana are used. Establish a shared understanding of communication conventions to avoid misinterpretations. ✅ Feedback Loop: Create an open channel for feedback. Encourage your team to seek clarification if something seems ambiguous. This proactive approach can avoid potential misunderstandings. What would you add to this list? 👇 #virtualleadership #hybridleadership #hybridwork #async

Every struggling new hire carries “baggage” from their last job. They just need a reset, not a rejection. A new hire once froze in a meeting when I asked for their thoughts. Later, he admitted, "In my last job, only managers spoke. I wasn’t sure if I should." That’s when I realized you’re not just hiring a person. You’re hiring their past workplace norms too. I now use a 3-phase framework to spot, reset, and reinforce workplace norms early. Phase 1: Surface the hidden sensitivities New hires won’t tell you what’s confusing. They’ll just hesitate. I try to uncover what they assume is “normal.” I look for clues: 🔍 Do they wait for permission instead of taking initiative? 🔍 Do they avoid pushing back in discussions? 🔍 Are they hesitant to ask for feedback? You can do this with an easy expectation reset exercise in onboarding: 1. "At your last job, how did decisions get made?" 2. "How was feedback typically given?" 3. "What was considered ‘overstepping’?" Their answers reveal hidden mismatches between their old playbook and your culture. Phase 2: Reset & align Don’t assume new hires will "figure it out". Make things explicit. I set clear norms: 1. Here, we challenge ideas openly, regardless of role. 2. We give real-time feedback—don’t wait for formal reviews. 3. Speed matters more than waiting for perfection. For this, use “Culture in Action” moments. → Instead of just telling them, model it in real time. → If they hesitate to push back, directly invite them to challenge something. → If they overthink feedback, normalize quick iteration—not perfection. Phase 3: Reinforce through real work Old habits don’t vanish. They resurface under stress. The real test is how they act when things get tough. Create intentional pressure moments: 1. Put them in decision-making roles early. 2. Assign them a project where feedback loops are fast. 3. Push them to own a meeting or initiative. Post-action debriefs help here: “I noticed you held back in that discussion—what was going through your mind?” This helps them reflect & adjust quickly, instead of carrying misaligned habits forward. Most onboarding processes focus on training skills. But resetting unspoken norms is just as critical (if not more). A struggling new hire isn’t always a bad fit. Sometimes, they’re just following the wrong playbook. What’s a past habit you had to unlearn in a new job?

A good onboarding plan conveys: People - Who do you need to know Personalities - How to collaborate well Process - How to do stuff Policies - What the rules are Politics - What the unwritten rules are Think about format. How should you best convey this information? How should it be referenced or reinforced? Self-paced resources? One-on-one convos? Group trainings? A combo? It's going to be different based on the role, what you need them to know, and when. And WHEN. What information must be conveyed immediately vs later? If later, how do you ensure "later" doesn't become "never?" When I was still leading teams, my go-to onboarding template was: 1️⃣ Pre-scheduling 1:1s with key stakeholders in the role, prioritized and spread out over the first 14-30 days. No agendas, just get to know you's. 2️⃣ Pre-scheduling 1:1 role-related chats with process/policy/outcome stakeholders. These stakeholders were strongly requested (required, if poss) to create a 1-2 guide for the new hire to have as a reference. The new hire was expected to read the reference BEFORE the meeting and come with questions. It's meant to be more of a conversation than a training. 3️⃣ Creating (if needed) a role wiki that tracks with the JD, naming stakeholders and linking to recommended tools/docs 4️⃣ Making sure the team has updated their "User Manuals," documents that explain their roles, a bit about their personalities, and working style. These manuals include the sections "When I'm At My Best" and "When I'm At My Worst" so preferences and quirks are explicit, instead of discovered slowly by accident. 5️⃣ Scheduling 2x weekly hour-long 1:1s for the first month, staggering down in frequency and duration as needed into the appropriate cadence for their role and growth trajectory. Sounds like a lot, but it's worth it to make sure you get the best out of someone. So many downstream problems and costs can be avoided with decent onboarding, and it doesn't have to be high-tech.